4-chloropheny chlorodibromomethyl sulfone | 129008-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloropheny chlorodibromomethyl sulfone
• 英文别名: chlorodibromomethyl-4-chlorophenyl sulfone；1-Chloro-4-[dibromo(chloro)methyl]sulfonylbenzene
• CAS: 129008-20-4
• 化学式: C₇H₄Br₂Cl₂O₂S
• 分子量: 382.888
• InChiKey: CRRMBRIARCYALE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloropheny chlorodibromomethyl sulfone 在 硫酸 、 硝酸 作用下， 以 水 为溶剂， 反应 2.0h， 以92%的产率得到chlorodibromomethyl-4-chloro-3-nitrophenyl sulfone
  参考文献：
  名称：

  New synthetic sulfone derivatives inhibit growth, adhesion and the leucine arylamidase APE2 gene expression of Candida albicans in vitro

  摘要：

  The successful preventing and effective treatment of invasive Candida albicans infections required research focused on synthesis of new classes of agents and antifungal activity studies. Bromodichlorom-ethyl-4-chloro-3-nitrophenyl sulfone (named compound 6); dichloromethyl-4-chloro-3-nitrophenyl sulfone (named 7); and chlorodibromomethyl-4-hydrazino-3-nitrophenyl sulfone (named 11) on inhibition of planktonic cells' growth, leucine arylamidase APE2 gene expression, and adhesion to epithelial cells were investigated. In vitro anti-Candida activities were determined against wild-types, and the morphogenesis mutants: Delta efg1 and Delta cph1. MICs of compounds 6, 7 and 11 (concentrated at 0.25-16 mu g/ml) were determined using the Clinical and Laboratory Standards Institute Broth Microdilution Method (M27-A3 Document). APE2 expression was analyzed using RT-PCR; relative quantification was normalized against ACT1 in cells growth in YEPD and on Caco-2 cell line. Adherence assay of C. albicans to Caco-2 was performed in 24-well-plate.The structure activity relationship suggested that sulfone containing hydrazine function at C-1 (compound 11) showed higher antifungal activity (cell inhibition% = 100 at 1-16 mu g/ml) than the remaining sulfones with chlorine at C-1. Delta cph1/Delta efg1 was highly sensitive to compound 11, while the sensitivity was reduced in Delta cph1/Delta efg1:: EFG1 (% = 100 at 16-fold higher concentration). Compound 11 significantly affected adherence to epithelium (P <= 0.05) and hyphae formation. The APE2 up-regulation plays role in sulfones' resistance on MAP kinase pathway. Either CPH1 or EFG1 play a role in the resistance mechanism in sulfones. The strain-dependent phenomenon is a factor in the sulfone resistance mechanism. Sulfones' mode of action was attributed to reduced virulence arsenal in terms of adhesiveness and pathogenic potential related to the APE2 expression and morphogenesis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.038
• 作为产物：
  描述：

  1-chloro-4-((dibromomethyl)sulfonyl)benzene 在 sodium chloride dihydrate 作用下， 以 水 为溶剂， 反应 4.0h， 以87%的产率得到4-chloropheny chlorodibromomethyl sulfone
  参考文献：
  名称：

  简单有效地合成三卤甲基和二卤硝基甲基芳基砜

  摘要：

  提出了一种制备具有相同或不同卤素的芳基三卤代甲基砜（活性杀生物剂）的方法。合成基于芳基甲基，芳基卤甲基或芳基硝基甲基砜与次卤酸钠的反应。该方法实施简单，不一定需要使用有机溶剂，并且选择性地以良好至优异的产率提供产物。值得注意的是，它允许制备迄今未知的具有三种不同卤素的苯基三卤代甲基砜：氟，氯和溴。

  DOI：

  10.1016/j.tetlet.2012.09.121

文献信息

• A simple and efficient synthesis of trihalomethyl and dihalonitromethyl aryl sulfones
  作者：Krzysztof M. Borys、Maciej D. Korzyński、Zbigniew Ochal

  DOI：10.1016/j.tetlet.2012.09.121

  日期：2012.11

  identical or different halogens is presented. The synthesis is based on the reaction of aryl methyl, aryl halomethyl, or aryl nitromethyl sulfones with sodium hypohalite. The method is simple in implementation, does not necessarily require the use of organic solvents, and selectively affords the products in good to excellent yields. Notably, it allows the preparation of the hitherto unknown phenyl trihalomethyl

  提出了一种制备具有相同或不同卤素的芳基三卤代甲基砜（活性杀生物剂）的方法。合成基于芳基甲基，芳基卤甲基或芳基硝基甲基砜与次卤酸钠的反应。该方法实施简单，不一定需要使用有机溶剂，并且选择性地以良好至优异的产率提供产物。值得注意的是，它允许制备迄今未知的具有三种不同卤素的苯基三卤代甲基砜：氟，氯和溴。
• New synthetic sulfone derivatives inhibit growth, adhesion and the leucine arylamidase APE2 gene expression of Candida albicans in vitro
  作者：Monika Staniszewska、Małgorzata Bondaryk、Zbigniew Ochal

  DOI：10.1016/j.bmc.2014.11.038

  日期：2015.1

  The successful preventing and effective treatment of invasive Candida albicans infections required research focused on synthesis of new classes of agents and antifungal activity studies. Bromodichlorom-ethyl-4-chloro-3-nitrophenyl sulfone (named compound 6); dichloromethyl-4-chloro-3-nitrophenyl sulfone (named 7); and chlorodibromomethyl-4-hydrazino-3-nitrophenyl sulfone (named 11) on inhibition of planktonic cells' growth, leucine arylamidase APE2 gene expression, and adhesion to epithelial cells were investigated. In vitro anti-Candida activities were determined against wild-types, and the morphogenesis mutants: Delta efg1 and Delta cph1. MICs of compounds 6, 7 and 11 (concentrated at 0.25-16 mu g/ml) were determined using the Clinical and Laboratory Standards Institute Broth Microdilution Method (M27-A3 Document). APE2 expression was analyzed using RT-PCR; relative quantification was normalized against ACT1 in cells growth in YEPD and on Caco-2 cell line. Adherence assay of C. albicans to Caco-2 was performed in 24-well-plate.The structure activity relationship suggested that sulfone containing hydrazine function at C-1 (compound 11) showed higher antifungal activity (cell inhibition% = 100 at 1-16 mu g/ml) than the remaining sulfones with chlorine at C-1. Delta cph1/Delta efg1 was highly sensitive to compound 11, while the sensitivity was reduced in Delta cph1/Delta efg1:: EFG1 (% = 100 at 16-fold higher concentration). Compound 11 significantly affected adherence to epithelium (P <= 0.05) and hyphae formation. The APE2 up-regulation plays role in sulfones' resistance on MAP kinase pathway. Either CPH1 or EFG1 play a role in the resistance mechanism in sulfones. The strain-dependent phenomenon is a factor in the sulfone resistance mechanism. Sulfones' mode of action was attributed to reduced virulence arsenal in terms of adhesiveness and pathogenic potential related to the APE2 expression and morphogenesis. (C) 2014 Elsevier Ltd. All rights reserved.